Artist painting a canvas in a sunlit studio with brushes in the foreground.

Arts & Culture

In The Florida Keys, creativity flows as freely as the tides. From galleries filled with local paintings and sculptures to theaters, dance, live music, and street festivals, the islands wear their artistry in full color. Key West has long lured writers, dreamers, and free spirits, while each destination brings its own twist—think outdoor art walks, history museums, and quirky roadside treasures. Whether you’re browsing studios or catching a play, culture here feels refreshingly unbuttoned, sun-soaked, and impossible to forget.

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Tennessee Williams Theatre

Tennessee Williams Theater — immersive theater & experiential performances in Key West, where storytelling becomes adventure.

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History of Diving Museum

Explore the fascinating history and evolution of diving at the History of Diving Museum!

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50

Key West

801 Bourbon Bar

801 Bourbon Bar is Key West's legendary LGBTQ nightclub at 801 Duval Street — home to the world-famous 801 Girls drag show, daily specialty cocktails, karaoke, bingo, and nonstop fun from noon to 4 AM every single day.

Key West

Key West Art and Historical Society

Explore two centuries of Key West history and art in a stunning historic landmark!

Key West

Mel Fisher Maritime Museum

Discover treasures and history at the Mel Fisher Maritime Museum in Key West!

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Florida Keys History & Discovery Center

Explore Florida Keys' rich history, marine life, and local art at this interactive discovery center.

Key West

90 Miles to Cuba

A weather-beaten shell-cleaning shack in the Historic Seaport, now packed with ships' portholes, old anchors, antique postcards of Cuba and paintings of a Key West that mostly is not there anymore. It opens a few afternoons a week, so check before you walk over.

Key West

Key West Sea Store - Antiques

A marine biologist who once curated the Key West Aquarium now builds picture frames out of retired lobster traps and sculpture out of old bottles. Bob Cerkleski's shop is on Fleming Street, and most of what is in it exists exactly once.

Key West

One Fish, Two Fish Studio

Art classes in a Whitehead Street studio a short walk from the Hemingway Home, working in watercolor, acrylic and mixed media. The studio also takes commissions, including pet portraits and murals.

Key West

Gingerbread Square Gallery

Key West’s oldest private art gallery, showcasing original works in a historic Victorian setting.

Key West

Key West Cultural Center and Veterans Museum and William Weech American Legion Post 168

The Key West Cultural Center & Veterans Museum is a community initiative dedicated to preserving and celebrating the history, culture, and military heritage of the Florida Keys through exhibits, educational programs, and cultural events.

Key West

Key West Impromptu Classical Concerts

Key West Impromptu — chamber music concert series in Key West, where world-class classical performance meets community spirit.

Key West

Abstracta

A small Duval Street gallery stocked with work that does not look like anybody else's on the street, including sculpture built out of reclaimed metal. It stays open into the evening, which makes it one of the few galleries you can browse after dinner.

Key West

Shade Ceramics and Shutter Photography

Shade & Shutter Key West is a serene, artisan gallery where handcrafted ceramics meet evocative nature photography.

Key West

St. Paul's Episcopal Church Key West

Founded in 1832 and the oldest congregation in Florida south of St. Augustine, St. Paul's Episcopal Church is one of Key West's most treasured historic landmarks, offering weekly worship, an annual concert series, and five on-grounds wedding and event venues at 401 Duval Street — all while undergoing a breathtaking historic restoration for its 200th anniversary in 2032.